# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4a
_database_code_depnum_ccdc_archive 'CCDC 1889029'
loop_
_audit_author_name
_audit_author_address
'Nagendra Sharma'
; National Institute of science Education and Research (NISER)-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;
_audit_creation_date             2018-02-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H14 N2 O4'
_chemical_formula_sum            'C12 H14 N2 O4'
_chemical_formula_weight         250.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C48 H56 N8 O16 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.8569(3)
_cell_length_b                   4.87510(10)
_cell_length_c                   18.1860(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.164(2)
_cell_angle_gamma                90.00
_cell_volume                     1216.08(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5845
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7890
_cell_measurement_theta_min      3.7650
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9626
_diffrn_reflns_theta_full        77.29
_diffrn_reflns_theta_max         77.29
_diffrn_reflns_theta_min         3.76
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -35.00   0.50    1.29    --  -38.50 -39.00 -72.00  138
  2  ω    -42.00  28.00   0.50    1.29    --  -38.50  39.00  81.00  140
  3  ω    -17.00  53.00   0.50    1.29    --   49.06 -39.00 -72.00  140
  4  ω     46.00 115.00   0.50    1.29    --   49.06  39.00  81.00  138
  5  ω     41.00 110.00   0.50    7.21    --  106.38 -39.00 -72.00  138
  6  ω    103.00 172.00   0.50    7.21    --  106.38  39.00  81.00  138
  7  ω    -42.00  28.00   0.50    1.29    --  -38.50  37.00-120.00  140
  8  ω    -42.00  28.00   0.50    1.29    --  -38.50  37.00 150.00  140
  9  ω     46.00 116.00   0.50    1.29    --   49.06  37.00-180.00  140
 10  ω    103.00 175.00   0.50    7.21    --  106.38  30.00 -30.00  144
 11  ω     42.00 122.00   0.50    7.21    --  106.38-125.00 -30.00  160
 12  ω     38.00 109.00   0.50    7.21    --  106.38 -94.00  60.00  142
 13  ω    102.00 171.00   0.50    7.21    --  106.38  45.00-150.00  138
 14  ω     83.00 171.00   0.50    7.21    --  106.38  77.00-180.00  176
 15  ω    102.00 171.00   0.50    7.21    --  106.38  45.00 -60.00  138
 16  ω     44.00 120.00   0.50    7.21    --  106.38 -61.00  30.00  152
 17  ω     42.00 111.00   0.50    7.21    --  106.38 -45.00  90.00  138
 18  ω     26.00 114.00   0.50    1.29    --   49.06  77.00-120.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0970269000
_diffrn_orient_matrix_UB_12      -0.1545366000
_diffrn_orient_matrix_UB_13      0.0207045000
_diffrn_orient_matrix_UB_21      0.0129887000
_diffrn_orient_matrix_UB_22      -0.0128092000
_diffrn_orient_matrix_UB_23      -0.0826651000
_diffrn_orient_matrix_UB_31      0.0550688000
_diffrn_orient_matrix_UB_32      0.2753473000
_diffrn_orient_matrix_UB_33      0.0078024000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_number_gt                2189
_reflns_number_total             2482
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0669P)²+0.1373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C6(H6), C3(H3), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O2 O 0.44657(7) 0.3252(2) 0.55574(5) 0.0508(3) Uani 1 d . . .
O1 O 0.84425(8) 0.4116(2) 0.74443(5) 0.0563(3) Uani 1 d . . .
O4 O 0.26070(7) 0.6317(2) 0.63022(7) 0.0618(3) Uani 1 d . . .
N1 N 0.69896(7) 0.3478(2) 0.64359(6) 0.0442(3) Uani 1 d . . .
H1 H 0.7081 0.2789 0.6876 0.053 Uiso 1 calc . . R
N2 N 0.51725(8) 0.6025(2) 0.64590(6) 0.0453(3) Uani 1 d . . .
H2 H 0.5686 0.6469 0.6759 0.054 Uiso 1 calc . . R
O3 O 0.35870(8) 0.3763(3) 0.71036(7) 0.0694(3) Uani 1 d . . .
C1 C 0.76406(8) 0.5346(2) 0.62764(6) 0.0383(3) Uani 1 d . . .
C9 C 0.51968(9) 0.3988(2) 0.59709(7) 0.0401(3) Uani 1 d . . .
C7 C 0.84730(9) 0.5580(3) 0.68782(7) 0.0432(3) Uani 1 d . . .
C11 C 0.34709(10) 0.5604(3) 0.66676(7) 0.0467(3) Uani 1 d . . .
C2 C 0.74925(10) 0.6822(3) 0.56165(7) 0.0466(3) Uani 1 d . . .
H2A H 0.6916 0.6412 0.5309 0.056 Uiso 1 calc . . R
C8 C 0.61518(9) 0.2511(3) 0.59427(8) 0.0474(3) Uani 1 d . . .
H8A H 0.6058 0.0589 0.6050 0.057 Uiso 1 calc . . R
H8B H 0.6301 0.2622 0.5438 0.057 Uiso 1 calc . . R
C10 C 0.42637(10) 0.7468(3) 0.64723(9) 0.0514(3) Uani 1 d . . .
H10A H 0.4057 0.8278 0.5988 0.062 Uiso 1 calc . . R
H10B H 0.4365 0.8943 0.6833 0.062 Uiso 1 calc . . R
C6 C 0.92779(10) 0.7341(3) 0.68419(9) 0.0564(4) Uani 1 d . . .
H6 H 0.9759 0.7224 0.7253 0.068 Uiso 1 calc . . R
C3 C 0.80651(12) 0.8817(3) 0.53392(9) 0.0576(4) Uani 1 d . . .
H3 H 0.7809 0.9528 0.4878 0.069 Uiso 1 calc . . R
C5 C 0.94824(12) 0.9180(4) 0.63181(11) 0.0669(4) Uani 1 d . . .
H5 H 1.0073 1.0098 0.6434 0.080 Uiso 1 calc . . R
C4 C 0.89481(13) 0.9895(4) 0.56405(10) 0.0667(4) Uani 1 d . . .
H4 H 0.9214 1.1232 0.5365 0.080 Uiso 1 calc . . R
C12 C 0.17918(12) 0.4705(5) 0.64695(12) 0.0792(5) Uani 1 d . . .
H12A H 0.1231 0.5085 0.6110 0.119 Uiso 1 calc . . GR
H12B H 0.1652 0.5168 0.6956 0.119 Uiso 1 calc . . GR
H12C H 0.1950 0.2792 0.6454 0.119 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C9 1.2265(15) . ?
O1 C7 1.2583(16) . ?
O4 C11 1.3303(17) . ?
O4 C12 1.443(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.3421(16) . ?
N1 C8 1.4416(16) . ?
N2 H2 0.8600 . ?
N2 C9 1.3357(17) . ?
N2 C10 1.4455(17) . ?
O3 C11 1.1934(17) . ?
C1 C7 1.4774(16) . ?
C1 C2 1.3896(17) . ?
C9 C8 1.5138(18) . ?
C7 C6 1.416(2) . ?
C11 C10 1.5065(19) . ?
C2 H2A 0.9300 . ?
C2 C3 1.394(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.367(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(3) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O4 C12 115.34(14) . . ?
C1 N1 H1 116.8 . . ?
C1 N1 C8 126.43(11) . . ?
C8 N1 H1 116.8 . . ?
C9 N2 H2 120.8 . . ?
C9 N2 C10 118.49(11) . . ?
C10 N2 H2 120.8 . . ?
N1 C1 C7 111.74(11) . . ?
N1 C1 C2 121.12(11) . . ?
C2 C1 C7 127.14(12) . . ?
O2 C9 N2 121.90(12) . . ?
O2 C9 C8 119.34(12) . . ?
N2 C9 C8 118.74(11) . . ?
O1 C7 C1 116.67(12) . . ?
O1 C7 C6 120.00(12) . . ?
C6 C7 C1 123.33(12) . . ?
O4 C11 C10 111.05(12) . . ?
O3 C11 O4 123.74(13) . . ?
O3 C11 C10 125.19(13) . . ?
C1 C2 H2A 114.7 . . ?
C1 C2 C3 130.70(13) . . ?
C3 C2 H2A 114.7 . . ?
N1 C8 C9 117.01(11) . . ?
N1 C8 H8A 108.0 . . ?
N1 C8 H8B 108.0 . . ?
C9 C8 H8A 108.0 . . ?
C9 C8 H8B 108.0 . . ?
H8A C8 H8B 107.3 . . ?
N2 C10 C11 112.14(11) . . ?
N2 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C7 C6 H6 113.9 . . ?
C5 C6 C7 132.26(14) . . ?
C5 C6 H6 113.9 . . ?
C2 C3 H3 115.0 . . ?
C4 C3 C2 130.08(15) . . ?
C4 C3 H3 115.0 . . ?
C6 C5 H5 114.9 . . ?
C6 C5 C4 130.23(15) . . ?
C4 C5 H5 114.9 . . ?
C3 C4 C5 126.22(15) . . ?
C3 C4 H4 116.9 . . ?
C5 C4 H4 116.9 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.723
_oxdiff_exptl_absorpt_empirical_full_min 0.246
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4f
_database_code_depnum_ccdc_archive 'CCDC 1889030'
loop_
_audit_author_name
_audit_author_address
'Nagendra Sharma'
; National Institute of science Education and Research (NISER)-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;
_audit_creation_date             2018-02-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H16 N2 O4'
_chemical_formula_sum            'C13 H16 N2 O4'
_chemical_formula_weight         264.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C52 H64 N8 O16 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.8433(12)
_cell_length_b                   11.6707(8)
_cell_length_c                   8.3343(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.376(7)
_cell_angle_gamma                90.00
_cell_volume                     1324.48(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2379
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9380
_cell_measurement_theta_min      4.9630
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9030
_diffrn_reflns_theta_full        77.06
_diffrn_reflns_theta_max         77.06
_diffrn_reflns_theta_min         4.99
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  26.00   0.50    0.83    --  -38.50  94.00 -67.00  194
  2  ω     -4.00  82.00   0.50    0.83    --   49.31 -94.00-178.00  172
  3  ω    101.00 175.00   0.50    3.00    --  106.38  94.00 -67.00  148
  4  ω     38.00 109.00   0.50    3.00    --  106.38 -94.00-178.00  142
  5  ω   -105.00 -35.00   0.50    0.83    --  -38.50 -37.00  30.00  140
  6  ω    -17.00  53.00   0.50    0.83    --   49.31 -37.00 -90.00  140
  7  ω     46.00 116.00   0.50    0.83    --   49.31  37.00-180.00  140
  8  ω     46.00 116.00   0.50    0.83    --   49.31  37.00 -60.00  140
  9  ω     94.00 171.00   0.50    3.00    --  106.38 125.00-120.00  154
 10  ω    102.00 171.00   0.50    3.00    --  106.38  45.00-180.00  138
 11  ω     38.00 110.00   0.50    3.00    --  106.38 -30.00-120.00  144
 12  ω    103.00 175.00   0.50    3.00    --  106.38  30.00 120.00  144
 13  ω     44.00 120.00   0.50    3.00    --  106.38 -61.00 -60.00  152
 14  ω     38.00 110.00   0.50    3.00    --  106.38 -30.00  90.00  144
 15  ω     42.00 111.00   0.50    3.00    --  106.38 -45.00 150.00  138
 16  ω    103.00 169.00   0.50    3.00    --  106.38  30.00  60.00  132
 17  ω    103.00 171.00   0.50    3.00    --  106.38  30.00  30.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0544759000
_diffrn_orient_matrix_UB_12      -0.0769095000
_diffrn_orient_matrix_UB_13      -0.1374374000
_diffrn_orient_matrix_UB_21      -0.0896406000
_diffrn_orient_matrix_UB_22      -0.0041605000
_diffrn_orient_matrix_UB_23      0.0858076000
_diffrn_orient_matrix_UB_31      -0.0424529000
_diffrn_orient_matrix_UB_32      0.1071697000
_diffrn_orient_matrix_UB_33      -0.0952036000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_number_gt                1639
_reflns_number_total             2695
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0767
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1895P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2220
_refine_ls_wR_factor_ref         0.2996
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C7(H7), C6(H6), C3(H3), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O2 O 0.3905(2) 0.22021(19) 0.3690(3) 0.0737(8) Uani 1 d . . .
O1 O 0.6189(2) 0.1253(2) 0.1401(3) 0.0762(8) Uani 1 d . . .
O4 O 0.0846(2) 0.4795(2) 0.3632(3) 0.0779(8) Uani 1 d . . .
N1 N 0.5324(2) 0.3009(2) 0.2249(3) 0.0633(8) Uani 1 d . . .
H1 H 0.5187 0.2300 0.2378 0.076 Uiso 1 calc . . R
N2 N 0.3257(2) 0.3945(2) 0.4036(3) 0.0657(8) Uani 1 d . . .
H2 H 0.3268 0.4664 0.3811 0.079 Uiso 1 calc . . R
O3 O 0.0534(2) 0.3633(3) 0.1488(3) 0.0939(10) Uani 1 d . . .
C1 C 0.6117(2) 0.3236(3) 0.1574(4) 0.0559(8) Uani 1 d . . .
C9 C 0.3912(2) 0.3245(3) 0.3544(4) 0.0598(9) Uani 1 d . . .
C8 C 0.4690(2) 0.3842(3) 0.2769(4) 0.0626(8) Uani 1 d . . .
H8A H 0.4376 0.4292 0.1842 0.075 Uiso 1 calc . . R
H8B H 0.5070 0.4357 0.3554 0.075 Uiso 1 calc . . R
C2 C 0.6589(3) 0.2178(3) 0.1138(4) 0.0629(9) Uani 1 d . . .
C7 C 0.6385(3) 0.4360(3) 0.1328(4) 0.0644(9) Uani 1 d . . .
H7 H 0.5971 0.4914 0.1638 0.077 Uiso 1 calc . . R
C12 C 0.0965(2) 0.3823(3) 0.2852(4) 0.0647(9) Uani 1 d . . .
C10 C 0.2532(3) 0.3517(3) 0.4940(4) 0.0690(9) Uani 1 d . . .
H10A H 0.2323 0.4141 0.5567 0.083 Uiso 1 calc . . R
H10B H 0.2836 0.2940 0.5705 0.083 Uiso 1 calc . . R
C11 C 0.1634(3) 0.3000(3) 0.3873(4) 0.0695(9) Uani 1 d . . .
H11A H 0.1853 0.2440 0.3157 0.083 Uiso 1 calc . . R
H11B H 0.1259 0.2593 0.4571 0.083 Uiso 1 calc . . R
C6 C 0.7168(3) 0.4786(3) 0.0697(4) 0.0728(10) Uani 1 d . . .
H6 H 0.7194 0.5581 0.0637 0.087 Uiso 1 calc . . R
C3 C 0.7470(3) 0.2177(3) 0.0486(5) 0.0718(10) Uani 1 d . . .
H3 H 0.7705 0.1447 0.0321 0.086 Uiso 1 calc . . R
C5 C 0.7922(3) 0.4220(4) 0.0138(5) 0.0822(11) Uani 1 d . . .
H5 H 0.8394 0.4674 -0.0216 0.099 Uiso 1 calc . . R
C4 C 0.8041(3) 0.3045(4) 0.0056(5) 0.0798(11) Uani 1 d . . .
H4 H 0.8590 0.2809 -0.0354 0.096 Uiso 1 calc . . R
C13 C 0.0143(4) 0.5608(4) 0.2807(6) 0.0933(13) Uani 1 d . . .
H13A H 0.0288 0.5770 0.1745 0.140 Uiso 1 calc . . GR
H13B H 0.0180 0.6304 0.3430 0.140 Uiso 1 calc . . GR
H13C H -0.0506 0.5293 0.2696 0.140 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C9 1.223(4) . ?
O1 C2 1.250(4) . ?
O4 C12 1.331(4) . ?
O4 C13 1.443(5) . ?
N1 H1 0.8600 . ?
N1 C1 1.347(5) . ?
N1 C8 1.429(4) . ?
N2 H2 0.8600 . ?
N2 C9 1.338(4) . ?
N2 C10 1.449(4) . ?
O3 C12 1.206(4) . ?
C1 C2 1.473(5) . ?
C1 C7 1.389(4) . ?
C9 C8 1.521(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 C3 1.422(6) . ?
C7 H7 0.9300 . ?
C7 C6 1.380(5) . ?
C12 C11 1.490(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.517(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.384(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.384(6) . ?
C4 H4 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O4 C13 117.4(3) . . ?
C1 N1 H1 117.1 . . ?
C1 N1 C8 125.8(3) . . ?
C8 N1 H1 117.1 . . ?
C9 N2 H2 119.4 . . ?
C9 N2 C10 121.3(3) . . ?
C10 N2 H2 119.4 . . ?
N1 C1 C2 111.7(3) . . ?
N1 C1 C7 120.4(3) . . ?
C7 C1 C2 127.8(3) . . ?
O2 C9 N2 124.0(3) . . ?
O2 C9 C8 121.1(3) . . ?
N2 C9 C8 114.9(3) . . ?
N1 C8 C9 109.8(3) . . ?
N1 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O1 C2 C1 116.8(3) . . ?
O1 C2 C3 120.2(3) . . ?
C3 C2 C1 123.0(3) . . ?
C1 C7 H7 114.9 . . ?
C6 C7 C1 130.2(4) . . ?
C6 C7 H7 114.9 . . ?
O4 C12 C11 112.9(3) . . ?
O3 C12 O4 122.3(3) . . ?
O3 C12 C11 124.8(4) . . ?
N2 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
N2 C10 C11 113.8(3) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C12 C11 C10 115.9(3) . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C7 C6 H6 114.8 . . ?
C7 C6 C5 130.3(4) . . ?
C5 C6 H6 114.8 . . ?
C2 C3 H3 113.8 . . ?
C4 C3 C2 132.3(4) . . ?
C4 C3 H3 113.8 . . ?
C6 C5 H5 116.8 . . ?
C4 C5 C6 126.4(4) . . ?
C4 C5 H5 116.8 . . ?
C3 C4 C5 129.7(4) . . ?
C3 C4 H4 115.1 . . ?
C5 C4 H4 115.1 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.153
_oxdiff_exptl_absorpt_empirical_full_min 0.367
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1889034'
loop_
_audit_author_name
_audit_author_address
'Nagendra Sharma'
; National Institute of science Education and Research (NISER)-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13  H16  N2  O4'
_chemical_formula_sum            'C13 H16 N2 O4'
_chemical_formula_weight         264.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8111(3)
_cell_length_b                   7.3881(3)
_cell_length_c                   27.5932(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1388.52(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2559
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6891
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17437
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.476
_diffrn_reflns_theta_max         25.450
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2559
_reflns_number_gt                1635
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'ShelXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.0726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(8)
_chemical_absolute_configuration rms
_refine_ls_number_reflns         2559
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.1528(4) 0.6740(3) 0.64983(7) 0.0729(7) Uani 1 1 d . . . . .
N1 N 0.1579(4) 0.7703(3) 0.55735(8) 0.0482(7) Uani 1 1 d . . . . .
H1 H 0.1597 0.8412 0.5821 0.058 Uiso 1 1 calc R U . . .
O1 O 0.1504(6) 1.1120(3) 0.55861(9) 0.0898(10) Uani 1 1 d . . . . .
O3 O 0.4708(5) 0.2804(5) 0.68442(10) 0.0973(11) Uani 1 1 d . . . . .
N2 N 0.1309(5) 0.3755(4) 0.63410(9) 0.0572(8) Uani 1 1 d . . . . .
H2 H 0.1260 0.2936 0.6120 0.069 Uiso 1 1 calc R U . . .
O4 O 0.3166(5) 0.3216(4) 0.75386(9) 0.0950(10) Uani 1 1 d . . . . .
C2 C 0.1580(5) 0.8482(4) 0.51357(10) 0.0432(7) Uani 1 1 d . . . . .
C9 C 0.1473(5) 0.5492(5) 0.62115(11) 0.0513(8) Uani 1 1 d . . . . .
C12 C 0.3246(8) 0.3079(5) 0.70595(12) 0.0629(10) Uani 1 1 d . . . . .
C3 C 0.1626(5) 0.7451(4) 0.47180(10) 0.0490(8) Uani 1 1 d . . . . .
H3 H 0.1675 0.6209 0.4771 0.059 Uiso 1 1 calc R U . . .
C8 C 0.1550(6) 0.5799(4) 0.56682(10) 0.0475(8) Uani 1 1 d . . . . .
H8A H 0.2718 0.5238 0.5535 0.057 Uiso 1 1 calc R U . . .
H8B H 0.0412 0.5255 0.5515 0.057 Uiso 1 1 calc R U . . .
C1 C 0.1533(5) 1.0479(4) 0.51682(12) 0.0574(8) Uani 1 1 d . . . . .
C4 C 0.1610(6) 0.7955(5) 0.42324(11) 0.0592(9) Uani 1 1 d . . . . .
H4 H 0.1647 0.7002 0.4013 0.071 Uiso 1 1 calc R U . . .
C5 C 0.1548(5) 0.9644(6) 0.40302(12) 0.0622(9) Uani 1 1 d . . . . .
H5 H 0.1551 0.9699 0.3694 0.075 Uiso 1 1 calc R U . . .
C7 C 0.1480(6) 1.1620(5) 0.47560(13) 0.0665(10) Uani 1 1 d . . . . .
H7 H 0.1434 1.2847 0.4831 0.080 Uiso 1 1 calc R U . . .
C10 C 0.1212(6) 0.3224(5) 0.68457(11) 0.0650(10) Uani 1 1 d . . . . .
H10 H 0.0482 0.4151 0.7025 0.078 Uiso 1 1 calc R U . . .
C6 C 0.1483(7) 1.1272(5) 0.42737(14) 0.0662(10) Uani 1 1 d . . . . .
H6 H 0.1433 1.2291 0.4076 0.079 Uiso 1 1 calc R U . . .
C11 C 0.0119(7) 0.1426(7) 0.68917(16) 0.1004(17) Uani 1 1 d . . . . .
H11A H 0.0058 0.1079 0.7227 0.151 Uiso 1 1 calc R U . . .
H11B H -0.1188 0.1559 0.6767 0.151 Uiso 1 1 calc R U . . .
H11C H 0.0801 0.0511 0.6711 0.151 Uiso 1 1 calc R U . . .
C13 C 0.5016(9) 0.3047(8) 0.77996(16) 0.125(2) Uani 1 1 d . . . . .
H13A H 0.4781 0.3167 0.8141 0.187 Uiso 1 1 calc R U . . .
H13B H 0.5584 0.1883 0.7735 0.187 Uiso 1 1 calc R U . . .
H13C H 0.5901 0.3979 0.7695 0.187 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C9 1.216(4) . ?
N1 C2 1.338(3) . ?
N1 C8 1.431(4) . ?
N1 H1 0.8600 . ?
O1 C1 1.247(4) . ?
O3 C12 1.177(5) . ?
N2 C9 1.336(4) . ?
N2 C10 1.448(4) . ?
N2 H2 0.8600 . ?
O4 C12 1.327(4) . ?
O4 C13 1.456(6) . ?
C2 C3 1.382(4) . ?
C2 C1 1.478(4) . ?
C9 C8 1.517(4) . ?
C12 C10 1.510(6) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C7 1.417(4) . ?
C4 C5 1.367(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C7 C6 1.356(4) . ?
C7 H7 0.9300 . ?
C10 C11 1.528(6) . ?
C10 H10 0.9800 . ?
C6 H6 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C8 126.0(2) . . ?
C2 N1 H1 117.0 . . ?
C8 N1 H1 117.0 . . ?
C9 N2 C10 121.4(3) . . ?
C9 N2 H2 119.3 . . ?
C10 N2 H2 119.3 . . ?
C12 O4 C13 116.8(4) . . ?
N1 C2 C3 121.1(3) . . ?
N1 C2 C1 112.0(3) . . ?
C3 C2 C1 126.9(3) . . ?
O2 C9 N2 123.8(3) . . ?
O2 C9 C8 121.9(3) . . ?
N2 C9 C8 114.3(3) . . ?
O3 C12 O4 123.4(4) . . ?
O3 C12 C10 126.2(3) . . ?
O4 C12 C10 110.3(4) . . ?
C2 C3 C4 131.0(3) . . ?
C2 C3 H3 114.5 . . ?
C4 C3 H3 114.5 . . ?
N1 C8 C9 109.2(3) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
O1 C1 C7 121.0(3) . . ?
O1 C1 C2 115.8(3) . . ?
C7 C1 C2 123.1(3) . . ?
C5 C4 C3 129.6(3) . . ?
C5 C4 H4 115.2 . . ?
C3 C4 H4 115.2 . . ?
C4 C5 C6 126.8(3) . . ?
C4 C5 H5 116.6 . . ?
C6 C5 H5 116.6 . . ?
C6 C7 C1 132.5(3) . . ?
C6 C7 H7 113.8 . . ?
C1 C7 H7 113.8 . . ?
N2 C10 C12 110.7(3) . . ?
N2 C10 C11 109.7(3) . . ?
C12 C10 C11 110.7(3) . . ?
N2 C10 H10 108.6 . . ?
C12 C10 H10 108.6 . . ?
C11 C10 H10 108.6 . . ?
C7 C6 C5 130.1(3) . . ?
C7 C6 H6 115.0 . . ?
C5 C6 H6 115.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C2 C3 -2.4(5) . . . . ?
C8 N1 C2 C1 177.7(3) . . . . ?
C10 N2 C9 O2 -1.0(6) . . . . ?
C10 N2 C9 C8 -179.9(3) . . . . ?
C13 O4 C12 O3 1.3(6) . . . . ?
C13 O4 C12 C10 178.2(4) . . . . ?
N1 C2 C3 C4 179.0(4) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 N1 C8 C9 -177.7(3) . . . . ?
O2 C9 C8 N1 -3.2(5) . . . . ?
N2 C9 C8 N1 175.8(3) . . . . ?
N1 C2 C1 O1 0.2(5) . . . . ?
C3 C2 C1 O1 -179.8(4) . . . . ?
N1 C2 C1 C7 -178.5(3) . . . . ?
C3 C2 C1 C7 1.6(6) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
O1 C1 C7 C6 -179.5(5) . . . . ?
C2 C1 C7 C6 -0.9(7) . . . . ?
C9 N2 C10 C12 -83.6(4) . . . . ?
C9 N2 C10 C11 153.9(4) . . . . ?
O3 C12 C10 N2 -24.6(5) . . . . ?
O4 C12 C10 N2 158.5(3) . . . . ?
O3 C12 C10 C11 97.3(5) . . . . ?
O4 C12 C10 C11 -79.6(4) . . . . ?
C1 C7 C6 C5 -0.3(9) . . . . ?
C4 C5 C6 C7 0.6(8) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.040

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4e
_database_code_depnum_ccdc_archive 'CCDC 1889033'
loop_
_audit_author_name
_audit_author_address
'Nagendra Sharma'
; National Institute of science Education and Research (NISER)-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16  H22  N2  O4'
_chemical_formula_sum            'C16 H22 N2 O4'
_chemical_formula_weight         306.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2453(2)
_cell_length_b                   9.1188(3)
_cell_length_c                   11.2435(4)
_cell_angle_alpha                77.692(2)
_cell_angle_beta                 86.278(2)
_cell_angle_gamma                86.449(2)
_cell_volume                     823.19(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4075
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      28.4

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6785
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13278
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.856
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4075
_reflns_number_gt                3093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'ShelXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.1080P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4075
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57885(13) 0.62368(11) 0.56018(10) 0.0684(3) Uani 1 1 d . . . . .
O2 O 0.03379(11) 0.77100(12) 0.23937(10) 0.0668(3) Uani 1 1 d . . . . .
N1 N 0.40091(12) 0.71163(11) 0.38126(10) 0.0491(3) Uani 1 1 d . . . . .
H1 H 0.4735 0.6389 0.3931 0.059 Uiso 1 1 calc R U . . .
N2 N 0.12743(13) 0.54368(12) 0.33905(10) 0.0504(3) Uani 1 1 d . . . . .
H2 H 0.2106 0.4893 0.3679 0.061 Uiso 1 1 calc R U . . .
O5 O -0.00376(16) 0.27472(13) 0.10433(10) 0.0798(4) Uani 1 1 d . . . . .
O4 O 0.11522(17) 0.22321(15) 0.27950(12) 0.0919(4) Uani 1 1 d . . . . .
C2 C 0.37361(13) 0.78876(12) 0.47073(11) 0.0416(3) Uani 1 1 d . . . . .
C12 C 0.14617(14) 0.68600(14) 0.28222(11) 0.0461(3) Uani 1 1 d . . . . .
C8 C 0.32082(14) 0.73821(14) 0.26712(11) 0.0464(3) Uani 1 1 d . . . . .
H8 H 0.3156 0.8469 0.2345 0.056 Uiso 1 1 calc R U . . .
C3 C 0.25793(15) 0.90719(14) 0.46235(12) 0.0495(3) Uani 1 1 d . . . . .
H3 H 0.2015 0.9273 0.3912 0.059 Uiso 1 1 calc R U . . .
C1 C 0.48178(15) 0.73210(13) 0.57211(12) 0.0478(3) Uani 1 1 d . . . . .
C9 C 0.42353(17) 0.66403(17) 0.17442(13) 0.0571(3) Uani 1 1 d . . . . .
H9 H 0.4416 0.5571 0.2110 0.069 Uiso 1 1 calc R U . . .
C15 C 0.02292(16) 0.30036(17) 0.21253(13) 0.0575(3) Uani 1 1 d . . . . .
C4 C 0.21252(16) 1.00077(16) 0.54305(14) 0.0581(3) Uani 1 1 d . . . . .
H4 H 0.1328 1.0749 0.5162 0.070 Uiso 1 1 calc R U . . .
C7 C 0.48018(18) 0.79272(16) 0.67828(13) 0.0583(3) Uani 1 1 d . . . . .
H7 H 0.5563 0.7465 0.7336 0.070 Uiso 1 1 calc R U . . .
C6 C 0.38723(19) 0.90666(17) 0.71430(13) 0.0624(4) Uani 1 1 d . . . . .
H6 H 0.4088 0.9232 0.7904 0.075 Uiso 1 1 calc R U . . .
C5 C 0.26623(17) 1.00121(18) 0.65541(14) 0.0616(4) Uani 1 1 d . . . . .
H5 H 0.2166 1.0720 0.6963 0.074 Uiso 1 1 calc R U . . .
C14 C -0.07770(17) 0.43286(19) 0.23885(15) 0.0640(4) Uani 1 1 d . . . . .
H14A H -0.1915 0.4090 0.2476 0.077 Uiso 1 1 calc R U . . .
H14B H -0.0649 0.5170 0.1703 0.077 Uiso 1 1 calc R U . . .
C13 C -0.03129(18) 0.47846(19) 0.35330(14) 0.0647(4) Uani 1 1 d . . . . .
H13A H -0.1129 0.5510 0.3748 0.078 Uiso 1 1 calc R U . . .
H13B H -0.0302 0.3909 0.4197 0.078 Uiso 1 1 calc R U . . .
C11 C 0.3346(2) 0.6765(3) 0.05843(15) 0.0929(6) Uani 1 1 d . . . . .
H11A H 0.2356 0.6241 0.0770 0.139 Uiso 1 1 calc R U . . .
H11B H 0.4024 0.6328 0.0011 0.139 Uiso 1 1 calc R U . . .
H11C H 0.3095 0.7805 0.0238 0.139 Uiso 1 1 calc R U . . .
C16 C 0.0754(3) 0.1414(2) 0.07414(19) 0.0938(6) Uani 1 1 d . . . . .
H16A H 0.0608 0.1412 -0.0099 0.141 Uiso 1 1 calc R U . . .
H16B H 0.0287 0.0542 0.1249 0.141 Uiso 1 1 calc R U . . .
H16C H 0.1895 0.1397 0.0872 0.141 Uiso 1 1 calc R U . . .
C10 C 0.5885(2) 0.7327(3) 0.1453(2) 0.0950(6) Uani 1 1 d . . . . .
H10A H 0.5738 0.8365 0.1057 0.142 Uiso 1 1 calc R U . . .
H10B H 0.6531 0.6797 0.0924 0.142 Uiso 1 1 calc R U . . .
H10C H 0.6429 0.7253 0.2195 0.142 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2571(16) . ?
O2 C12 1.2252(14) . ?
N1 C2 1.3453(16) . ?
N1 C8 1.4489(15) . ?
N1 H1 0.8600 . ?
N2 C12 1.3323(16) . ?
N2 C13 1.4562(17) . ?
N2 H2 0.8600 . ?
O5 C15 1.3212(17) . ?
O5 C16 1.438(2) . ?
O4 C15 1.1930(17) . ?
C2 C3 1.3876(17) . ?
C2 C1 1.4784(16) . ?
C12 C8 1.5323(17) . ?
C8 C9 1.5414(19) . ?
C8 H8 0.9800 . ?
C3 C4 1.3921(19) . ?
C3 H3 0.9300 . ?
C1 C7 1.4175(19) . ?
C9 C11 1.517(2) . ?
C9 C10 1.520(2) . ?
C9 H9 0.9800 . ?
C15 C14 1.494(2) . ?
C4 C5 1.366(2) . ?
C4 H4 0.9300 . ?
C7 C6 1.368(2) . ?
C7 H7 0.9300 . ?
C6 C5 1.383(2) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C14 C13 1.512(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C8 126.84(10) . . ?
C2 N1 H1 116.6 . . ?
C8 N1 H1 116.6 . . ?
C12 N2 C13 121.23(11) . . ?
C12 N2 H2 119.4 . . ?
C13 N2 H2 119.4 . . ?
C15 O5 C16 116.45(13) . . ?
N1 C2 C3 121.64(11) . . ?
N1 C2 C1 111.54(10) . . ?
C3 C2 C1 126.81(12) . . ?
O2 C12 N2 123.39(12) . . ?
O2 C12 C8 120.52(12) . . ?
N2 C12 C8 116.03(10) . . ?
N1 C8 C12 113.00(10) . . ?
N1 C8 C9 109.90(10) . . ?
C12 C8 C9 111.12(10) . . ?
N1 C8 H8 107.5 . . ?
C12 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C2 C3 C4 130.54(12) . . ?
C2 C3 H3 114.7 . . ?
C4 C3 H3 114.7 . . ?
O1 C1 C7 120.12(11) . . ?
O1 C1 C2 116.10(11) . . ?
C7 C1 C2 123.78(12) . . ?
C11 C9 C10 110.30(15) . . ?
C11 C9 C8 111.02(12) . . ?
C10 C9 C8 111.10(13) . . ?
C11 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
O4 C15 O5 122.47(16) . . ?
O4 C15 C14 125.77(15) . . ?
O5 C15 C14 111.75(12) . . ?
C5 C4 C3 130.41(13) . . ?
C5 C4 H4 114.8 . . ?
C3 C4 H4 114.8 . . ?
C6 C7 C1 131.83(13) . . ?
C6 C7 H7 114.1 . . ?
C1 C7 H7 114.1 . . ?
C7 C6 C5 130.22(14) . . ?
C7 C6 H6 114.9 . . ?
C5 C6 H6 114.9 . . ?
C4 C5 C6 126.37(14) . . ?
C4 C5 H5 116.8 . . ?
C6 C5 H5 116.8 . . ?
C15 C14 C13 112.61(13) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
N2 C13 C14 112.54(12) . . ?
N2 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C2 C3 0.77(19) . . . . ?
C8 N1 C2 C1 -178.37(11) . . . . ?
C13 N2 C12 O2 0.48(19) . . . . ?
C13 N2 C12 C8 -176.72(11) . . . . ?
C2 N1 C8 C12 -74.19(15) . . . . ?
C2 N1 C8 C9 161.07(12) . . . . ?
O2 C12 C8 N1 128.74(12) . . . . ?
N2 C12 C8 N1 -53.97(14) . . . . ?
O2 C12 C8 C9 -107.18(14) . . . . ?
N2 C12 C8 C9 70.11(13) . . . . ?
N1 C2 C3 C4 -179.43(13) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
N1 C2 C1 O1 -0.39(16) . . . . ?
C3 C2 C1 O1 -179.47(12) . . . . ?
N1 C2 C1 C7 179.73(12) . . . . ?
C3 C2 C1 C7 0.6(2) . . . . ?
N1 C8 C9 C11 174.27(13) . . . . ?
C12 C8 C9 C11 48.45(16) . . . . ?
N1 C8 C9 C10 -62.59(16) . . . . ?
C12 C8 C9 C10 171.59(13) . . . . ?
C16 O5 C15 O4 4.5(2) . . . . ?
C16 O5 C15 C14 -174.41(14) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
O1 C1 C7 C6 -178.91(15) . . . . ?
C2 C1 C7 C6 1.0(2) . . . . ?
C1 C7 C6 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C7 C6 C5 C4 -0.4(3) . . . . ?
O4 C15 C14 C13 9.7(2) . . . . ?
O5 C15 C14 C13 -171.44(12) . . . . ?
C12 N2 C13 C14 79.39(17) . . . . ?
C15 C14 C13 N2 69.89(17) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1889031'
loop_
_audit_author_name
_audit_author_address
'Nagendra Sharma'
; National Institute of science Education and Research (NISER)-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 N2 O4'
_chemical_formula_sum            'C15 H20 N2 O4'
_chemical_formula_weight         292.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8029(5)
_cell_length_b                   10.6573(5)
_cell_length_c                   10.8703(5)
_cell_angle_alpha                115.740(4)
_cell_angle_beta                 99.231(3)
_cell_angle_gamma                103.722(4)
_cell_volume                     754.32(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2967
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      26.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6459
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10451
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2967
_reflns_number_gt                1802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'ShelXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2967
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6531(2) -0.08178(15) 0.50938(15) 0.0342(4) Uani 1 1 d . . . . .
O2 O 0.7403(2) 0.52527(16) 0.98429(16) 0.0397(4) Uani 1 1 d . . . . .
O4 O 0.4307(2) 0.63112(16) 0.69752(16) 0.0397(4) Uani 1 1 d . . . . .
O3 O 0.6887(2) 0.57406(18) 0.69324(19) 0.0520(5) Uani 1 1 d . . . . .
N1 N 0.7542(2) 0.17135(18) 0.73179(18) 0.0299(4) Uani 1 1 d . . . . .
H1 H 0.6836 0.0877 0.7171 0.036 Uiso 1 1 calc R U . . .
N2 N 0.5522(2) 0.35464(18) 0.76197(19) 0.0309(4) Uani 1 1 d . . . . .
H2 H 0.5229 0.2664 0.6914 0.037 Uiso 1 1 calc R U . . .
C2 C 0.8127(3) 0.1720(2) 0.6214(2) 0.0269(5) Uani 1 1 d . . . . .
C1 C 0.7539(3) 0.0216(2) 0.4984(2) 0.0292(5) Uani 1 1 d . . . . .
C14 C 0.5401(3) 0.5561(2) 0.7118(2) 0.0327(5) Uani 1 1 d . . . . .
C8 C 0.7994(3) 0.2985(2) 0.8723(2) 0.0320(5) Uani 1 1 d . . . . .
H8 H 0.9312 0.3551 0.9000 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6951(3) 0.4034(2) 0.8774(2) 0.0304(5) Uani 1 1 d . . . . .
C13 C 0.4468(3) 0.4453(2) 0.7528(2) 0.0339(5) Uani 1 1 d . . . . .
H13A H 0.4269 0.4982 0.8446 0.041 Uiso 1 1 calc R U . . .
H13B H 0.3267 0.3819 0.6824 0.041 Uiso 1 1 calc R U . . .
C3 C 0.9105(3) 0.3048(2) 0.6310(2) 0.0358(6) Uani 1 1 d . . . . .
H3 H 0.9272 0.3895 0.7159 0.043 Uiso 1 1 calc R U . . .
C7 C 0.8112(3) -0.0102(3) 0.3731(2) 0.0376(6) Uani 1 1 d . . . . .
H7 H 0.7729 -0.1108 0.3073 0.045 Uiso 1 1 calc R U . . .
C4 C 0.9875(3) 0.3314(3) 0.5339(3) 0.0411(6) Uani 1 1 d . . . . .
H4 H 1.0462 0.4310 0.5637 0.049 Uiso 1 1 calc R U . . .
C6 C 0.9118(3) 0.0799(3) 0.3320(3) 0.0449(6) Uani 1 1 d . . . . .
H6 H 0.9308 0.0306 0.2436 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7738(3) 0.2501(2) 0.9848(2) 0.0419(6) Uani 1 1 d . . . . .
H9 H 0.8127 0.3411 1.0773 0.050 Uiso 1 1 calc R U . . .
C5 C 0.9905(3) 0.2342(3) 0.4017(3) 0.0463(7) Uani 1 1 d . . . . .
H5 H 1.0509 0.2750 0.3536 0.056 Uiso 1 1 calc R U . . .
C11 C 0.5712(4) 0.1663(3) 0.9574(3) 0.0513(7) Uani 1 1 d . . . . .
H11A H 0.4975 0.2246 0.9498 0.077 Uiso 1 1 calc R U . . .
H11B H 0.5294 0.0733 0.8699 0.077 Uiso 1 1 calc R U . . .
H11C H 0.5593 0.1484 1.0354 0.077 Uiso 1 1 calc R U . . .
C15 C 0.5028(4) 0.7400(2) 0.6555(3) 0.0496(7) Uani 1 1 d . . . . .
H15A H 0.4150 0.7879 0.6481 0.074 Uiso 1 1 calc R U . . .
H15B H 0.6172 0.8126 0.7262 0.074 Uiso 1 1 calc R U . . .
H15C H 0.5240 0.6914 0.5646 0.074 Uiso 1 1 calc R U . . .
C10 C 0.8993(4) 0.1645(3) 0.9982(3) 0.0601(8) Uani 1 1 d . . . . .
H10A H 1.0247 0.2214 1.0152 0.090 Uiso 1 1 calc R U . . .
H10B H 0.8913 0.1466 1.0767 0.090 Uiso 1 1 calc R U . . .
H10C H 0.8614 0.0715 0.9112 0.090 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.257(2) . ?
O2 C12 1.225(2) . ?
O4 C14 1.335(3) . ?
O4 C15 1.450(2) . ?
O3 C14 1.193(2) . ?
N1 C2 1.352(3) . ?
N1 C8 1.448(3) . ?
N1 H1 0.8600 . ?
N2 C12 1.341(3) . ?
N2 C13 1.433(3) . ?
N2 H2 0.8600 . ?
C2 C3 1.389(3) . ?
C2 C1 1.470(3) . ?
C1 C7 1.427(3) . ?
C14 C13 1.508(3) . ?
C8 C12 1.520(3) . ?
C8 C9 1.542(3) . ?
C8 H8 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C7 C6 1.366(3) . ?
C7 H7 0.9300 . ?
C4 C5 1.366(3) . ?
C4 H4 0.9300 . ?
C6 C5 1.395(3) . ?
C6 H6 0.9300 . ?
C9 C10 1.518(3) . ?
C9 C11 1.528(3) . ?
C9 H9 0.9800 . ?
C5 H5 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O4 C15 115.54(17) . . ?
C2 N1 C8 126.05(17) . . ?
C2 N1 H1 117.0 . . ?
C8 N1 H1 117.0 . . ?
C12 N2 C13 121.88(19) . . ?
C12 N2 H2 119.1 . . ?
C13 N2 H2 119.1 . . ?
N1 C2 C3 120.6(2) . . ?
N1 C2 C1 111.75(17) . . ?
C3 C2 C1 127.67(19) . . ?
O1 C1 C7 120.2(2) . . ?
O1 C1 C2 116.77(18) . . ?
C7 C1 C2 123.04(18) . . ?
O3 C14 O4 124.5(2) . . ?
O3 C14 C13 125.7(2) . . ?
O4 C14 C13 109.84(18) . . ?
N1 C8 C12 114.19(18) . . ?
N1 C8 C9 111.23(17) . . ?
C12 C8 C9 110.31(18) . . ?
N1 C8 H8 106.9 . . ?
C12 C8 H8 106.9 . . ?
C9 C8 H8 106.9 . . ?
O2 C12 N2 122.8(2) . . ?
O2 C12 C8 120.3(2) . . ?
N2 C12 C8 116.88(19) . . ?
N2 C13 C14 112.88(18) . . ?
N2 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N2 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C2 C3 C4 130.3(2) . . ?
C2 C3 H3 114.8 . . ?
C4 C3 H3 114.8 . . ?
C6 C7 C1 131.9(2) . . ?
C6 C7 H7 114.1 . . ?
C1 C7 H7 114.1 . . ?
C5 C4 C3 130.2(2) . . ?
C5 C4 H4 114.9 . . ?
C3 C4 H4 114.9 . . ?
C7 C6 C5 130.1(2) . . ?
C7 C6 H6 114.9 . . ?
C5 C6 H6 114.9 . . ?
C10 C9 C11 112.5(2) . . ?
C10 C9 C8 111.5(2) . . ?
C11 C9 C8 112.10(19) . . ?
C10 C9 H9 106.7 . . ?
C11 C9 H9 106.7 . . ?
C8 C9 H9 106.7 . . ?
C4 C5 C6 126.4(2) . . ?
C4 C5 H5 116.8 . . ?
C6 C5 H5 116.8 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C2 C3 -6.9(3) . . . . ?
C8 N1 C2 C1 175.07(19) . . . . ?
N1 C2 C1 O1 3.6(3) . . . . ?
C3 C2 C1 O1 -174.3(2) . . . . ?
N1 C2 C1 C7 -174.27(19) . . . . ?
C3 C2 C1 C7 7.9(3) . . . . ?
C15 O4 C14 O3 0.4(3) . . . . ?
C15 O4 C14 C13 -178.92(18) . . . . ?
C2 N1 C8 C12 75.9(3) . . . . ?
C2 N1 C8 C9 -158.4(2) . . . . ?
C13 N2 C12 O2 3.1(3) . . . . ?
C13 N2 C12 C8 -178.20(16) . . . . ?
N1 C8 C12 O2 -169.19(17) . . . . ?
C9 C8 C12 O2 64.7(2) . . . . ?
N1 C8 C12 N2 12.0(2) . . . . ?
C9 C8 C12 N2 -114.1(2) . . . . ?
C12 N2 C13 C14 80.1(2) . . . . ?
O3 C14 C13 N2 -2.7(3) . . . . ?
O4 C14 C13 N2 176.64(17) . . . . ?
N1 C2 C3 C4 178.0(2) . . . . ?
C1 C2 C3 C4 -4.3(4) . . . . ?
O1 C1 C7 C6 176.8(2) . . . . ?
C2 C1 C7 C6 -5.4(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C1 C7 C6 C5 -0.2(4) . . . . ?
N1 C8 C9 C10 60.9(2) . . . . ?
C12 C8 C9 C10 -171.31(19) . . . . ?
N1 C8 C9 C11 -66.3(3) . . . . ?
C12 C8 C9 C11 61.5(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C7 C6 C5 C4 2.2(4) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4j
_database_code_depnum_ccdc_archive 'CCDC 1889032'
loop_
_audit_author_name
_audit_author_address
'Nagendra Sharma'
; National Institute of science Education and Research (NISER)-Bhubaneswar
India
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-07
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H22 N2 O4)'
_chemical_formula_sum            'C40 H44 N4 O8'
_chemical_formula_weight         708.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C42 H46 N10 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5709(3)
_cell_length_b                   9.7281(3)
_cell_length_c                   11.5654(3)
_cell_angle_alpha                72.921(3)
_cell_angle_beta                 79.751(3)
_cell_angle_gamma                68.981(3)
_cell_volume                     957.66(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4851
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0220
_cell_measurement_theta_min      3.9800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14809
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.457
_diffrn_reflns_theta_min         4.967
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  27.00   0.50    2.00    --  -38.50  80.00-118.00  180
  2  ω    100.00 172.00   0.50    8.00    --  106.38  80.00-118.00  144
  3  ω     41.00 131.00   0.50    8.00    --  106.38 -80.00 118.00  180
  4  ω    -42.00  28.00   0.50    2.00    --  -38.50  37.00  90.00  140
  5  ω    -42.00  28.00   0.50    2.00    --  -38.50  37.00 150.00  140
  6  ω      2.00  85.00   0.50    2.00    --   49.31 -99.00 -90.00  166
  7  ω     38.00 112.00   0.50    2.00    --   49.31  57.00  30.00  148
  8  ω    -16.00  74.00   0.50    2.00    --   49.31 -80.00 118.00  180
  9  ω    -13.00  61.00   0.50    2.00    --   49.31 -57.00 -60.00  148
 10  ω    -17.00  53.00   0.50    2.00    --   49.31 -37.00-180.00  140
 11  ω     42.00 111.00   0.50    8.00    --  106.38 -45.00  90.00  138
 12  ω     98.00 175.00   0.50    8.00    --  106.38  15.00  90.00  154
 13  ω     98.00 175.00   0.50    8.00    --  106.38  15.00   0.00  154
 14  ω     38.00 109.00   0.50    8.00    --  106.38 -94.00  90.00  142
 15  ω    102.00 171.00   0.50    8.00    --  106.38  45.00  30.00  138
 16  ω     38.00 115.00   0.50    8.00    --  106.38 -15.00-120.00  154
 17  ω     42.00 122.00   0.50    8.00    --  106.38-125.00 150.00  160
 18  ω     93.00 169.00   0.50    8.00    --  106.38  61.00   0.00  152
 19  ω     44.00 120.00   0.50    8.00    --  106.38 -61.00-180.00  152
 20  ω     42.00 130.00   0.50    8.00    --  106.38 -77.00 -90.00  176
 21  ω     38.00 109.00   0.50    8.00    --  106.38 -94.00 -90.00  142
 22  ω     44.00 120.00   0.50    8.00    --  106.38 -61.00 -90.00  152
 23  ω     42.00 122.00   0.50    8.00    --  106.38-125.00-150.00  160
 24  ω     44.00 120.00   0.50    8.00    --  106.38 -61.00 -30.00  152
 25  ω     83.00 171.00   0.50    8.00    --  106.38  77.00  30.00  176
 26  ω    103.00 175.00   0.50    8.00    --  106.38  30.00 120.00  144
 27  ω     38.00 109.00   0.50    8.00    --  106.38 -94.00  30.00  142
 28  ω     26.00 114.00   0.50    2.00    --   49.31  77.00-150.00  176
 29  ω     38.00 112.00   0.50    2.00    --   49.31  57.00 120.00  148
 30  ω     26.00  82.00   0.50    2.00    --   49.31  77.00 150.00  112
 31  ω     26.00 114.00   0.50    2.00    --   49.31  77.00 -60.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0318920000
_diffrn_orient_matrix_UB_12      -0.1233862000
_diffrn_orient_matrix_UB_13      0.1201521000
_diffrn_orient_matrix_UB_21      0.1427189000
_diffrn_orient_matrix_UB_22      0.0355994000
_diffrn_orient_matrix_UB_23      0.0055338000
_diffrn_orient_matrix_UB_31      -0.0924479000
_diffrn_orient_matrix_UB_32      0.1192171000
_diffrn_orient_matrix_UB_33      0.0712764000
_diffrn_oxdiff_ac3_digest_frames 
;
017af7a8de20b329e83ecfb84e1404bd5604766fd68
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01103c27ccfa19bfc0a9e30fa1c608d1e1909e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2470
_reflns_number_total             3838
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0667
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1232P)²+0.0584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2030
_refine_ls_wR_factor_ref         0.2267
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C6(H6), C2(H2A), C5(H5), C3(H3), C4(H4), C11(H11), C15(H15),
 C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37660(18) -0.11547(17) 0.52661(18) 0.0857(5) Uani 1 1 d . . . . .
N1 N 0.26986(18) 0.16665(19) 0.51294(17) 0.0637(5) Uani 1 1 d . . . . .
H1 H 0.345456 0.100790 0.550625 0.076 Uiso 1 1 calc R . . . .
O2 O 0.1655(2) 0.55651(18) 0.3740(2) 0.1014(7) Uani 1 1 d . . . . .
N2 N 0.3963(2) 0.3913(2) 0.3575(2) 0.0822(6) Uani 1 1 d . . . . .
H2 H 0.457175 0.301526 0.384585 0.099 Uiso 1 1 calc R . . . .
C7 C 0.2047(2) 0.1182(2) 0.44656(18) 0.0564(5) Uani 1 1 d . . . . .
C1 C 0.2693(2) -0.0473(2) 0.4605(2) 0.0636(5) Uani 1 1 d . . . . .
C6 C 0.0904(2) 0.2197(2) 0.3741(2) 0.0668(5) Uani 1 1 d . . . . .
H6 H 0.066511 0.320953 0.374782 0.080 Uiso 1 1 calc R . . . .
C16 C 0.2592(2) 0.4328(2) 0.4117(2) 0.0725(6) Uani 1 1 d . . . . .
C8 C 0.2241(2) 0.3200(2) 0.5268(2) 0.0691(6) Uani 1 1 d . . . . .
H8 H 0.115230 0.353353 0.546583 0.083 Uiso 1 1 calc R . . . .
C2 C 0.2144(3) -0.1285(3) 0.4059(2) 0.0743(6) Uani 1 1 d . . . . .
H2A H 0.263345 -0.232951 0.425456 0.089 Uiso 1 1 calc R . . . .
C5 C 0.0060(3) 0.1947(3) 0.3006(2) 0.0774(6) Uani 1 1 d . . . . .
H5 H -0.062942 0.281986 0.258382 0.093 Uiso 1 1 calc R . . . .
C10 C 0.2696(3) 0.2210(3) 0.7496(3) 0.0833(7) Uani 1 1 d . . . . .
C3 C 0.1027(3) -0.0820(3) 0.3296(2) 0.0829(7) Uani 1 1 d . . . . .
H3 H 0.088036 -0.159848 0.307085 0.099 Uiso 1 1 calc R . . . .
C4 C 0.0086(3) 0.0620(3) 0.2810(2) 0.0822(7) Uani 1 1 d . . . . .
H4 H -0.059896 0.069534 0.229712 0.099 Uiso 1 1 calc R . . . .
O4 O 0.7766(3) 0.4707(4) 0.0541(3) 0.1490(11) Uani 1 1 d . . . . .
C9 C 0.2986(3) 0.3244(3) 0.6312(3) 0.0842(7) Uani 1 1 d . . . . .
H9A H 0.406146 0.297224 0.610586 0.101 Uiso 1 1 calc R . . . .
H9B H 0.262787 0.427766 0.640318 0.101 Uiso 1 1 calc R . . . .
C17 C 0.4458(3) 0.4936(3) 0.2537(3) 0.0915(8) Uani 1 1 d . . . . .
H17A H 0.455377 0.576048 0.279262 0.110 Uiso 1 1 calc R . . . .
H17B H 0.371071 0.537266 0.194809 0.110 Uiso 1 1 calc R . . . .
C11 C 0.1275(4) 0.2467(4) 0.8113(3) 0.1023(9) Uani 1 1 d . . . . .
H11 H 0.048664 0.330958 0.777906 0.123 Uiso 1 1 calc R . . . .
O3 O 0.5581(5) 0.6372(4) 0.0321(4) 0.1791(15) Uani 1 1 d . . . . .
C18 C 0.5908(3) 0.4145(4) 0.1964(3) 0.1019(9) Uani 1 1 d . . . . .
H18A H 0.582212 0.331005 0.171726 0.122 Uiso 1 1 calc R . . . .
H18B H 0.666545 0.372851 0.254339 0.122 Uiso 1 1 calc R . . . .
C19 C 0.6372(4) 0.5234(5) 0.0876(4) 0.1114(10) Uani 1 1 d . . . . .
C15 C 0.3830(4) 0.0939(4) 0.8023(4) 0.1151(11) Uani 1 1 d . . . . .
H15 H 0.479551 0.073951 0.763807 0.138 Uiso 1 1 calc R . . . .
C12 C 0.1004(5) 0.1509(6) 0.9203(4) 0.1299(13) Uani 1 1 d . . . . .
H12 H 0.004957 0.171392 0.960700 0.156 Uiso 1 1 calc R . . . .
C13 C 0.2154(8) 0.0253(6) 0.9685(4) 0.1474(17) Uani 1 1 d . . . . .
H13 H 0.197696 -0.041037 1.041453 0.177 Uiso 1 1 calc R . . . .
C14 C 0.3566(7) -0.0035(5) 0.9099(5) 0.1466(17) Uani 1 1 d . . . . .
H14 H 0.434372 -0.089122 0.943133 0.176 Uiso 1 1 calc R . . . .
C20 C 0.8057(8) 0.5924(8) -0.0621(5) 0.211(3) Uani 1 1 d . . . . .
H20A H 0.850551 0.544570 -0.127522 0.316 Uiso 1 1 calc GR . . . .
H20B H 0.872267 0.637090 -0.045549 0.316 Uiso 1 1 calc GR . . . .
H20C H 0.712227 0.670197 -0.084383 0.316 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.254(3) . ?
N1 H1 0.8600 . ?
N1 C7 1.339(3) . ?
N1 C8 1.445(3) . ?
O2 C16 1.225(3) . ?
N2 H2 0.8600 . ?
N2 C16 1.324(3) . ?
N2 C17 1.446(4) . ?
C7 C1 1.473(3) . ?
C7 C6 1.393(3) . ?
C1 C2 1.417(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.393(3) . ?
C16 C8 1.528(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.526(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.372(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.366(4) . ?
C10 C9 1.490(4) . ?
C10 C11 1.392(4) . ?
C10 C15 1.381(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
O4 C19 1.279(4) . ?
O4 C20 1.566(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.471(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(5) . ?
O3 C19 1.168(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.503(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.371(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(7) . ?
C14 H14 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 H1 117.2 . . ?
C7 N1 C8 125.66(17) . . ?
C8 N1 H1 117.2 . . ?
C16 N2 H2 119.3 . . ?
C16 N2 C17 121.4(2) . . ?
C17 N2 H2 119.3 . . ?
N1 C7 C1 112.15(17) . . ?
N1 C7 C6 121.01(19) . . ?
C6 C7 C1 126.84(19) . . ?
O1 C1 C7 115.9(2) . . ?
O1 C1 C2 120.7(2) . . ?
C2 C1 C7 123.4(2) . . ?
C7 C6 H6 114.7 . . ?
C5 C6 C7 130.7(2) . . ?
C5 C6 H6 114.7 . . ?
O2 C16 N2 122.2(3) . . ?
O2 C16 C8 121.1(2) . . ?
N2 C16 C8 116.64(19) . . ?
N1 C8 C16 113.12(18) . . ?
N1 C8 H8 108.0 . . ?
N1 C8 C9 110.66(19) . . ?
C16 C8 H8 108.0 . . ?
C9 C8 C16 109.0(2) . . ?
C9 C8 H8 108.0 . . ?
C1 C2 H2A 113.9 . . ?
C3 C2 C1 132.1(2) . . ?
C3 C2 H2A 113.9 . . ?
C6 C5 H5 114.9 . . ?
C4 C5 C6 130.2(2) . . ?
C4 C5 H5 114.9 . . ?
C11 C10 C9 121.8(3) . . ?
C15 C10 C9 121.2(3) . . ?
C15 C10 C11 117.1(3) . . ?
C2 C3 H3 114.9 . . ?
C2 C3 C4 130.1(2) . . ?
C4 C3 H3 114.9 . . ?
C5 C4 C3 126.5(2) . . ?
C5 C4 H4 116.8 . . ?
C3 C4 H4 116.8 . . ?
C19 O4 C20 105.4(4) . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 C8 114.0(2) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N2 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
N2 C17 C18 111.4(2) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
C17 C18 C19 110.0(3) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
O4 C19 C18 111.4(4) . . ?
O3 C19 O4 121.9(4) . . ?
O3 C19 C18 126.4(4) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.5(4) . . ?
C14 C15 H15 119.2 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.568
_oxdiff_exptl_absorpt_empirical_full_min 0.334
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7190 14537 550 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.2810 0 550 nmt 0.9728 0.0661 0.0026 -0.0696 1.0235 0.0017 -0.0273 0.0143
1.0011

_twin_special_details            
;
Component 2 rotated by 3.6639° 
 around [0.01 0.03 -1.00] (reciprocal) or [0.09 0.33 -0.94] (direct)
;
